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Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity

A new flavanol derivative, (2R,3R)-3-acetoxy-7-hydroxy-3′,4′-methylenedioxyflavan (1), was co-isolated from the rhizomes of Zephyranthes ajax Hort. with the following seven known compounds: 7-hydroxyflavan (2), 7,4′-dihydroxyflavan (3), 7,4′-dihydroxy-8-methylflavan (4), 7,3′-dihydroxy-4′-methoxyfla...

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Autores principales: Nguyen, Khan Viet, Ho, Duc Viet, Le, Nhan Trong, Van Phan, Kiem, Heinämäki, Jyrki, Raal, Ain, Nguyen, Hoai Thi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7747562/
https://www.ncbi.nlm.nih.gov/pubmed/33335132
http://dx.doi.org/10.1038/s41598-020-78785-2
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author Nguyen, Khan Viet
Ho, Duc Viet
Le, Nhan Trong
Van Phan, Kiem
Heinämäki, Jyrki
Raal, Ain
Nguyen, Hoai Thi
author_facet Nguyen, Khan Viet
Ho, Duc Viet
Le, Nhan Trong
Van Phan, Kiem
Heinämäki, Jyrki
Raal, Ain
Nguyen, Hoai Thi
author_sort Nguyen, Khan Viet
collection PubMed
description A new flavanol derivative, (2R,3R)-3-acetoxy-7-hydroxy-3′,4′-methylenedioxyflavan (1), was co-isolated from the rhizomes of Zephyranthes ajax Hort. with the following seven known compounds: 7-hydroxyflavan (2), 7,4′-dihydroxyflavan (3), 7,4′-dihydroxy-8-methylflavan (4), 7,3′-dihydroxy-4′-methoxyflavan (5), 5,4′-dihydroxy-7-methoxy-6-methylflavan (6), 7-hydroxy-3′,4′-methylenedioxyflavanone (7) and haemanthamine (8). Their structures were elucidated by combining 1D-/2D-NMR, CD, UV and HRESIMS data, and comparisons with reported data in literature were made. Among these known compounds, 2, 3, 4, 6 and 7 were isolated from the genus Zephyranthes for the first time. In addition, the cytotoxicity assay indicated that compound 8 has potent cytotoxic activity against human hepatocellular carcinoma (the HepG2 cell line), human lung carcinoma (the SK-LU-1 cell line), human carcinoma in the mouth (the KB cell line), human colon carcinoma (the SW480 cell line) and human stomach gastric adenocarcinoma (the AGS cell line), with IC(50) values ranging from 4.4 to 11.3 µM. This is the first study reporting the cytotoxicity of compound 8 against the SK-LU-1 cancer cell lines.
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spelling pubmed-77475622020-12-18 Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity Nguyen, Khan Viet Ho, Duc Viet Le, Nhan Trong Van Phan, Kiem Heinämäki, Jyrki Raal, Ain Nguyen, Hoai Thi Sci Rep Article A new flavanol derivative, (2R,3R)-3-acetoxy-7-hydroxy-3′,4′-methylenedioxyflavan (1), was co-isolated from the rhizomes of Zephyranthes ajax Hort. with the following seven known compounds: 7-hydroxyflavan (2), 7,4′-dihydroxyflavan (3), 7,4′-dihydroxy-8-methylflavan (4), 7,3′-dihydroxy-4′-methoxyflavan (5), 5,4′-dihydroxy-7-methoxy-6-methylflavan (6), 7-hydroxy-3′,4′-methylenedioxyflavanone (7) and haemanthamine (8). Their structures were elucidated by combining 1D-/2D-NMR, CD, UV and HRESIMS data, and comparisons with reported data in literature were made. Among these known compounds, 2, 3, 4, 6 and 7 were isolated from the genus Zephyranthes for the first time. In addition, the cytotoxicity assay indicated that compound 8 has potent cytotoxic activity against human hepatocellular carcinoma (the HepG2 cell line), human lung carcinoma (the SK-LU-1 cell line), human carcinoma in the mouth (the KB cell line), human colon carcinoma (the SW480 cell line) and human stomach gastric adenocarcinoma (the AGS cell line), with IC(50) values ranging from 4.4 to 11.3 µM. This is the first study reporting the cytotoxicity of compound 8 against the SK-LU-1 cancer cell lines. Nature Publishing Group UK 2020-12-17 /pmc/articles/PMC7747562/ /pubmed/33335132 http://dx.doi.org/10.1038/s41598-020-78785-2 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Nguyen, Khan Viet
Ho, Duc Viet
Le, Nhan Trong
Van Phan, Kiem
Heinämäki, Jyrki
Raal, Ain
Nguyen, Hoai Thi
Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title_full Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title_fullStr Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title_full_unstemmed Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title_short Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity
title_sort flavonoids and alkaloids from the rhizomes of zephyranthes ajax hort. and their cytotoxicity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7747562/
https://www.ncbi.nlm.nih.gov/pubmed/33335132
http://dx.doi.org/10.1038/s41598-020-78785-2
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